Roots and Roses: Sleepy Hollow High School Marks 35 Years of a Tradition That Connects Generations

On May 21, 2026, the Public Schools of the Tarrytowns celebrated one of its most beloved traditions: the 35th Annual Rose Ceremony.

Held at Sleepy Hollow High School, the ceremony brought together first graders from Tappan Hill School and members of the SHHS Class of 2026 for a symbolic exchange reflecting both the beginning and culmination of the K–12 experience. In the fall, seniors welcomed the first graders with roses as they embarked on their educational journey. This spring, the tradition came full circle as the first graders returned those roses to the seniors, marking the start of a new chapter for the soon-to-be graduates.

In her opening remarks, SHHS Principal Dr. Deborah Brand noted that the ceremony represented far more than a simple exchange of flowers.

"Students, throughout our lives there are certain moments that invite us to pause, reflect, and recognize the memorable experiences that have shaped who we are," said Dr. Brand. "Today is one of those moments."

Dr. Brand described the Rose Ceremony as a tradition "deeply special to this district," adding that it reminds the community "that education is not just about classrooms and science. It's about connection, continuity, and community."

Class of 2026 Advisor Jon Cincotta reflected on the shared experiences that connect both groups of students — despite the years between them — as he addressed the crowd.

"Our first graders are beginning their journey through the school system, while our seniors are preparing to leave the nest to begin the next chapter of their lives," he said. "Though separated by age, their experiences are similar — they will build friendships, experience love and heartbreak, and encounter problems that require resilience, courage, and growth. And through it all, they will always share one thing: the connection to our school community."

For Senior Class President Ava Mendez, the ceremony carried deep personal meaning. Reflecting on the years that shaped her, she spoke about finally understanding a lesson her father shared with her growing up.

"When I was little, my dad used to say it 'takes a village,'" she said. "As I sit here today, I finally understand what he meant."

Turning toward the first graders seated across from the senior class, she encouraged them to savor the moments ahead. "Enjoy every field day, class birthday party, every recess, every band and chorus concert, and every club meeting — because it goes by fast," she said.

As first graders carefully handed roses to the seniors, some students embraced, others wiped away tears, and families looked on proudly. Seniors knelt beside the younger students, smiling as they accepted roses from children who, not long ago, were standing exactly where they once stood.

For some seniors, the ceremony stirred memories of their own first Rose Ceremony years earlier. Senior Vielka De la Cruz recalled attending as a first grader on her birthday, and felt a wave of emotions receiving the rose as a senior.

"I started crying, I was sad because it's the end of my high school career," she shared.

Senior Benjamin Meyer said the spring ceremony felt even more emotional than the fall tradition.

"It hit a little harder than the fall ceremony, knowing that it's actually over this time," he said. "Getting that rose as a senior was definitely a great moment. It was beautiful for this community, and it just shows how genuine Sleepy Hollow is with all their students, their schools, and their community."

As the ceremony concluded, seniors left with roses in hand and graduation on the horizon, while the district's youngest learners walked away with a glimpse of what lies ahead. Like the roses exchanged between them, the tradition serves as a reminder that growth takes time, that memories stay rooted long after the moment passes, and that every journey through the Public Schools of the Tarrytowns is held together by community.